Depolymerization of glycosaminoglycuronans into di- and higher molecular-weight oligo-saccharides: improved preparation of N-acetyldermosine and oligomeric N-acetylchondrosines.
Nonsulfated di- to octadeca-saccharides having 2-acetamido-2-deoxy-D-galactose at the reducing end were prepared, in 81% yield, by treatment of chondroitin 6-sulfate (pyridinium salt) with dimethyl sulfoxide containing 10% of water for 14 h at 90 degrees. N-Acetylchondrosine and N-acetyldermosine were obtained from dermatan sulfate of rooster comb, in 30% and 38% yields, respectively, by solvolysis with dimethyl sulfoxide, containing 10% of water, for 30 h at 105 degrees. Hyaluronic acid was also depolymerized by the same solvent in the presence of an equimolar amount of pyridinium sulfate or chloride per disaccharide unit to give reducing di- and higher molecular weight oligo-saccharides. The results of solvolytic desulfation and depolymerization are compared with those of the conventional methods by acid hydrolysis.
D000818:Animals; D002807:Chondroitin / Q000031:analogs & derivatives; D002809:Chondroitin Sulfates; D003129:Comb and Wattles / Q000032:analysis; D004121:Dimethyl Sulfoxide; D004187:Disaccharides; D006025:Glycosaminoglycans; D008297:Male; D008970:Molecular Weight; D009844:Oligosaccharides / Q000032:analysis*; D012867:Skin / Q000032:analysis; D013552:Swine
D004187:Disaccharides; D006025:Glycosaminoglycans; D009844:Oligosaccharides; C033269:N-acetylchondrosine; C033268:N-acetyldermosine; D002807:Chondroitin; D002809:Chondroitin Sulfates; D004121:Dimethyl Sulfoxide